A novel one-pot synthesis of ferrocenyl-substituted 1,2,4-oxadiazoles

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• 作者：Metin Zora ; ^{zora@metu.edu.tr" class="auth_mail} ; Arif Kivrak ; Yilmaz Kelgokmen
• 关键词：1 ; 2 ; 4-Oxadiazole ; Amidoxime ; Ferrocene ; 3-Ferrocenylpropynal ; Conjugate addition ; Cyclization
• 刊名：Journal of Organometallic Chemistry
• 出版年：1 June, 2014
• 年：2014
• 卷：759
• 期：Complete
• 页码：67-73
• 全文大小：835 K

文摘

One-pot synthesis of 5-ferrocenyl-1,2,4-oxadiazoles via the reaction between 3-ferrocenylpropynal and amidoximes is described. 3-Ferrocenylpropynal reacts with a variety of amidoximes in the presence of KOH in refluxing dioxane to afford a broad range of 5-ferrocenyl-1,2,4-oxadiazole derivatives. The reaction first produces the corresponding conjugate addition product which, upon cyclization and rearrangement, yields the targeted 1,2,4-oxadiazole. The reaction appears to be general for a diversity of amidoximes and tolerates the presence of aryl groups with electron-withdrawing and electron-donating substituents.